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Palladium(II)-catalyzed three-component coupling reaction initiated by acetoxypalladation of alkynes: an efficient route to gamma,delta-unsaturated carbonyls.
Org Lett. 2002 Oct 31; 4(22):3903-6.OL

Abstract

[formula: see text] A divalent palladium-catalyzed coupling reaction of electron-deficient alkynes and acrolein or MVK (methyl vinyl ketone) was developed. The reaction provides an efficient method to synthesize gamma,delta-unsaturated carbonyls. A mechanism involving acetoxypalladation of alkyne, followed by insertion of alkene and protonolysis of the C-Pd bond, is proposed. The protonolysis of the carbon-palladium bond with the assistance of bidentate nitrogen containing ligands is the key step in this tandem reaction.

Authors+Show Affiliations

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

12599488

Citation

Zhao, Ligang, and Xiyan Lu. "Palladium(II)-catalyzed Three-component Coupling Reaction Initiated By Acetoxypalladation of Alkynes: an Efficient Route to Gamma,delta-unsaturated Carbonyls." Organic Letters, vol. 4, no. 22, 2002, pp. 3903-6.
Zhao L, Lu X. Palladium(II)-catalyzed three-component coupling reaction initiated by acetoxypalladation of alkynes: an efficient route to gamma,delta-unsaturated carbonyls. Org Lett. 2002;4(22):3903-6.
Zhao, L., & Lu, X. (2002). Palladium(II)-catalyzed three-component coupling reaction initiated by acetoxypalladation of alkynes: an efficient route to gamma,delta-unsaturated carbonyls. Organic Letters, 4(22), 3903-6.
Zhao L, Lu X. Palladium(II)-catalyzed Three-component Coupling Reaction Initiated By Acetoxypalladation of Alkynes: an Efficient Route to Gamma,delta-unsaturated Carbonyls. Org Lett. 2002 Oct 31;4(22):3903-6. PubMed PMID: 12599488.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium(II)-catalyzed three-component coupling reaction initiated by acetoxypalladation of alkynes: an efficient route to gamma,delta-unsaturated carbonyls. AU - Zhao,Ligang, AU - Lu,Xiyan, PY - 2003/2/26/pubmed PY - 2003/2/26/medline PY - 2003/2/26/entrez SP - 3903 EP - 6 JF - Organic letters JO - Org Lett VL - 4 IS - 22 N2 - [formula: see text] A divalent palladium-catalyzed coupling reaction of electron-deficient alkynes and acrolein or MVK (methyl vinyl ketone) was developed. The reaction provides an efficient method to synthesize gamma,delta-unsaturated carbonyls. A mechanism involving acetoxypalladation of alkyne, followed by insertion of alkene and protonolysis of the C-Pd bond, is proposed. The protonolysis of the carbon-palladium bond with the assistance of bidentate nitrogen containing ligands is the key step in this tandem reaction. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/12599488/Palladium_II__catalyzed_three_component_coupling_reaction_initiated_by_acetoxypalladation_of_alkynes:_an_efficient_route_to_gammadelta_unsaturated_carbonyls_ DB - PRIME DP - Unbound Medicine ER -
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